Natural Coumarin Isomers with Dramatically Different AIE Properties: Mechanism and Application

Aggregation-induced emission luminogens (AIEgens) are of great importance in optoelectronics and biomedical fields. However, the popular design philosophy by combining rotors with traditional fluorophores limits the imagination and structural diversity of AIEgens. Inspired by the fluorescent roots o...

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Bibliographic Details
Published in:ACS central science 2023-05, Vol.9 (5), p.883-891
Main Authors: Chen, Shan-Shan, Wang, Haoran, Wu, Bo, Li, Qiyao, Gong, Junyi, Zhao, Yun-Li, Zhao, Yun, Xiao, Xia, Lam, Jacky W. Y., Zhao, Zheng, Luo, Xiao-Dong, Tang, Ben Zhong
Format: Article
Language:English
Subjects:
Aggregates
Aqueous solutions
Biocompatibility
Chemical compounds
Coumarin
Crystal structure
Emissions control
Energy transfer
Fluorescence
Fluorophores
Herbal medicine
Isomers
Medicinal plants
Natural products
Optoelectronics
Rotors
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Summary:Aggregation-induced emission luminogens (AIEgens) are of great importance in optoelectronics and biomedical fields. However, the popular design philosophy by combining rotors with traditional fluorophores limits the imagination and structural diversity of AIEgens. Inspired by the fluorescent roots of the medicinal plant Toddalia asiatica, we discovered two unconventional rotor-free AIEgens, 5-methoxyseselin (5-MOS) and 6-methoxyseselin (6-MOS). Interestingly, a slight structural difference of the coumarin isomers leads to completely contrary fluorescent properties upon aggregation in aqueous media. Further mechanism investigation indicates that 5-MOS forms different extents of aggregates with the assistance of protonic solvents, leading to electron/energy transfer, which is responsible for its unique AIE feature, i.e., reduced emission in aqueous media but enhanced emission in crystal. Meanwhile, for 6-MOS, the conventional restriction of the intramolecular motion (RIM) mechanism is responsible for its AIE feature. More interestingly, the unique water-sensitive fluorescence property of 5-MOS enables its successful application for wash-free mitochondria imaging. This work not only demonstrates an ingenious tactic to seek new AIEgens from natural fluorescent species but also benefits the structure design and application exploration of next-generation AIEgens.
ISSN:2374-7943
2374-7951
DOI:10.1021/acscentsci.3c00012